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Gene Review

FA-C18:3  -  Linolenic acid content

Sus scrofa

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Disease relevance of FA-C18:3


High impact information on FA-C18:3

  • This assembly might be promoted by recently identified 1-(3'-O-acyl)-beta-D-glucosyl-N-(omega-hydroxyacyl)sphingosines, which have 30- and 32-carbon hydroxy acids as amides and linoleic acid esterified to glucose [6].
  • In UVB-irradiated guinea pig skin, topical applications of the pseudo-acylceramides with linoleic acid immediately after the exposure significantly reduced epidermal hyperplasia, secondary to markedly diminished barrier disruption, whereas linoleic acid itself did not [1].
  • In this study, drug-treated cells that were rendered sensitive to killing by anti-Forssman antibody plus GPC, but not antitumor antibody plus GPC, were inhibited in their incorporation of saturated (palmitic or stearic acid), but not an unsaturated, fatty acid (linoleic acid) [7].
  • Linoleic acid (18:2n-6) and alpha-linolenic acid (18:3n-3) are polyunsaturated fatty acids that are essential for mammalian nutrition, because mammals lack the desaturases required for synthesis of Delta12 (n-6) and n-3 fatty acids [8].
  • In addition, the white adipose tissue of transgenic pigs contained approximately 20% more linoleic acid (18:2n-6) than that of wild-type pigs [8].

Chemical compound and disease context of FA-C18:3


Biological context of FA-C18:3


Anatomical context of FA-C18:3

  • Levels of linoleic acid (18:2n-6) in adipocytes that had differentiated in vitro from cells derived from the transgenic pigs were approximately 10 times higher than those from wild-type pigs [8].
  • When endothelial cells were exposed to peroxidized linoleic acid, it caused lysis of the cells at doses 1,000-fold lower than effective doses of H2O2 [16].
  • In liver and kidney membranes, anisotropy parameters and the acute effect of ethanol correlated inversely with levels of linoleic acid and directly with levels of arachidonic and docosahexaenoic acids and their specific double bonds [17].
  • The 12/15-lipoxygenase expressed in macrophages is capable of oxygenating linoleic acid esterified to cholesterol in the LDL particle, and thus this enzyme is presumed to initiate LDL oxidation [18].
  • Effect of cytochrome c on the linoleic acid-degrading activity of porcine leukocyte 12-lipoxygenase [15].

Associations of FA-C18:3 with chemical compounds


Physical interactions of FA-C18:3


Regulatory relationships of FA-C18:3


Other interactions of FA-C18:3


Analytical, diagnostic and therapeutic context of FA-C18:3


  1. Pseudo-acylceramide with linoleic acid produces selective recovery of diminished cutaneous barrier function in essential fatty acid-deficient rats and has an inhibitory effect on epidermal hyperplasia. Imokawa, G., Yada, Y., Higuchi, K., Okuda, M., Ohashi, Y., Kawamata, A. J. Clin. Invest. (1994) [Pubmed]
  2. Glucogenic and ketogenic capacities of lard, safflower oil, and triumdecanoin in fasting rats. Anderson, R.L., Boggs, R.W. J. Nutr. (1975) [Pubmed]
  3. Conjugated linoleic acid in humans: regulation of adiposity and insulin sensitivity. Brown, J.M., McIntosh, M.K. J. Nutr. (2003) [Pubmed]
  4. The role of methyl-linoleic acid epoxide and diol metabolites in the amplified toxicity of linoleic acid and polychlorinated biphenyls to vascular endothelial cells. Slim, R., Hammock, B.D., Toborek, M., Robertson, L.W., Newman, J.W., Morisseau, C.H., Watkins, B.A., Saraswathi, V., Hennig, B. Toxicol. Appl. Pharmacol. (2001) [Pubmed]
  5. Production of hydroxy fatty acid (10-hydroxy-12(Z)-octadecenoic acid) by Lactobacillus plantarum from linoleic acid and its cardiac effects to guinea pig papillary muscles. Yamada, Y., Uemura, H., Nakaya, H., Sakata, K., Takatori, T., Nagao, M., Iwase, H., Iwadate, K. Biochem. Biophys. Res. Commun. (1996) [Pubmed]
  6. Glycolipids in mammalian epidermis: structure and function in the water barrier. Wertz, P.W., Downing, D.T. Science (1982) [Pubmed]
  7. Correlation between the ability of tumor cells to incorporate specific fatty acids and their sensitivity to killing by a specific antibody plus guinea pig complement. Schlager, S.I., Ohanian, S.H., Borsos, T. J. Natl. Cancer Inst. (1978) [Pubmed]
  8. Functional expression of a Delta12 fatty acid desaturase gene from spinach in transgenic pigs. Saeki, K., Matsumoto, K., Kinoshita, M., Suzuki, I., Tasaka, Y., Kano, K., Taguchi, Y., Mikami, K., Hirabayashi, M., Kashiwazaki, N., Hosoi, Y., Murata, N., Iritani, A. Proc. Natl. Acad. Sci. U.S.A. (2004) [Pubmed]
  9. Linoleic acid and alpha-linolenic acid lightens ultraviolet-induced hyperpigmentation of the skin. Ando, H., Ryu, A., Hashimoto, A., Oka, M., Ichihashi, M. Arch. Dermatol. Res. (1998) [Pubmed]
  10. Select dietary fatty acids attenuate cardiopulmonary dysfunction during acute lung injury in pigs. Murray, M.J., Kumar, M., Gregory, T.J., Banks, P.L., Tazelaar, H.D., DeMichele, S.J. Am. J. Physiol. (1995) [Pubmed]
  11. Quantitative trait loci mapping for fatty acid contents in the backfat on porcine chromosomes 1, 13, and 18. Lee, C., Chung, Y., Kim, J.H. Mol. Cells (2003) [Pubmed]
  12. Linoleic acid activates nuclear transcription factor-kappa B (NF-kappa B) and induces NF-kappa B-dependent transcription in cultured endothelial cells. Hennig, B., Toborek, M., Joshi-Barve, S., Barger, S.W., Barve, S., Mattson, M.P., McClain, C.J. Am. J. Clin. Nutr. (1996) [Pubmed]
  13. Zinc protects against apoptosis of endothelial cells induced by linoleic acid and tumor necrosis factor alpha. Meerarani, P., Ramadass, P., Toborek, M., Bauer, H.C., Bauer, H., Hennig, B. Am. J. Clin. Nutr. (2000) [Pubmed]
  14. Linoleic acid induces relaxation and hyperpolarization of the pig coronary artery. Pomposiello, S.I., Alva, M., Wilde, D.W., Carretero, O.A. Hypertension (1998) [Pubmed]
  15. Effect of cytochrome c on the linoleic acid-degrading activity of porcine leukocyte 12-lipoxygenase. Iwase, H., Sakurada, K., Hatanaka, K., Kobayashi, M., Takatori, T. Free Radic. Biol. Med. (2000) [Pubmed]
  16. Exogenous oxidants initiate hydrolysis of endothelial cell inositol phospholipids. Shasby, D.M., Yorek, M., Shasby, S.S. Blood (1988) [Pubmed]
  17. Effects of ethanol feeding on liver, kidney and jejunal membranes of micropigs. Villanueva, J., Chandler, C.J., Shimasaki, N., Tang, A.B., Nakamura, M., Phinney, S.D., Halsted, C.H. Hepatology (1994) [Pubmed]
  18. Low density lipoprotein receptor-related protein-mediated membrane translocation of 12/15-lipoxygenase is required for oxidation of low density lipoprotein by macrophages. Zhu, H., Takahashi, Y., Xu, W., Kawajiri, H., Murakami, T., Yamamoto, M., Iseki, S., Iwasaki, T., Hattori, H., Yoshimoto, T. J. Biol. Chem. (2003) [Pubmed]
  19. Dietary fat saturation modifies the metabolism of LDL subfractions in guinea pigs. Fernandez, M.L., Abdel-Fattah, G., McNamara, D.J. Arterioscler. Thromb. (1993) [Pubmed]
  20. A diet containing myristoleic plus palmitoleic acids elevates plasma cholesterol in young growing swine. Smith, D.R., Knabe, D.A., Cross, H.R., Smith, S.B. Lipids (1996) [Pubmed]
  21. Interaction of glucose and long chain fatty acids (C18) on antioxidant defences and free radical damage in porcine vascular smooth muscle cells in vitro. Hamilton, J.S., Powell, L.A., McMaster, C., McMaster, D., Trimble, E.R. Diabetologia (2003) [Pubmed]
  22. The importance of lipid type in the diet after burn injury. Alexander, J.W., Saito, H., Trocki, O., Ogle, C.K. Ann. Surg. (1986) [Pubmed]
  23. Cholesterol attenuates linoleic acid-induced endothelial cell activation. Meerarani, P., Smart, E.J., Toborek, M., Boissonneault, G.A., Hennig, B. Metab. Clin. Exp. (2003) [Pubmed]
  24. Cellular glutathione status modulates polychlorinated biphenyl-induced stress response and apoptosis in vascular endothelial cells. Slim, R., Toborek, M., Robertson, L.W., Lehmler, H.J., Hennig, B. Toxicol. Appl. Pharmacol. (2000) [Pubmed]
  25. Dietary linoleic acid increases and palmitic acid decreases hepatic LDL receptor protein and mRNA abundance in young pigs. Mustad, V.A., Ellsworth, J.L., Cooper, A.D., Kris-Etherton, P.M., Etherton, T.D. J. Lipid Res. (1996) [Pubmed]
  26. Effect of vitamin E on linoleic acid-mediated induction of peroxisomal enzymes in cultured porcine endothelial cells. Hennig, B., Boissonneault, G.A., Chow, C.K., Wang, Y., Matulionis, D.H., Glauert, H.P. J. Nutr. (1990) [Pubmed]
  27. Linoleic acid-induced endothelial activation: role of calcium and peroxynitrite signaling. Saraswathi, V., Wu, G., Toborek, M., Hennig, B. J. Lipid Res. (2004) [Pubmed]
  28. Suppression of lipid peroxidation in adrenal microsomes following ACTH administration to guinea pigs. Burczynski, J.M., Hayes, J.R., Voigt, J.M., Longhurst, P.A., Colby, H.D. J. Endocrinol. (2001) [Pubmed]
  29. Oxidized low-density lipoproteins delay endothelial wound healing: lack of effect of vitamin E. Boissonneault, G.A., Wang, Y., Chung, B.H. Ann. Nutr. Metab. (1995) [Pubmed]
  30. Effects of unsaturated fatty acids on calcium-activated potassium current in gastric myocytes of guinea pigs. Zheng, H.F., Li, X.L., Jin, Z.Y., Sun, J.B., Li, Z.L., Xu, W.X. World J. Gastroenterol. (2005) [Pubmed]
  31. Modulation of eosinophil chemotactic activities to leukotriene B4 by n-3 polyunsaturated fatty acids. Kikuchi, S., Sakamoto, T., Ishikawa, C., Yazawa, K., Torii, S. Prostaglandins Leukot. Essent. Fatty Acids (1998) [Pubmed]
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